With the busy fall season approaching, we thought we’d take a closer look at where some of Chicago’s most expensive condos currently on the market are listed, and what each of these lavish and luxurious units have to offer. Not surprisingly, No. 9 Walton, Waldorf Astoria Chicago, and Trump Tower feature the three highest priced condos right now, each boasting a price tag of well over $12 million. Somewhat unexpected, just two condos over at Vista Tower are among some of the Windy City’s 25 most expensive units on the market right now, which is the same number of units you’ll see listed over at The Palmolive in that same category.

The spectacular new One Bennett Park condo tower also features a couple condos in the $6 million price range, and you’ll also see the sprawling 6,597 square foot penthouse over at the Ritz Carlton Residences still on the open market as well, which is asking $9,500,000.

And while we’re talking penthouses, #PH1 over at 900 West Washington is also still available for $5,679,999, and the penthouse over at the chic new 61 West Erie development, which has four bedrooms, four bathrooms, and 5,800 square feet of living space is also on the market with an asking price of $5,850,000.

Browse Chicago's Most Expensive Condos Currently on the Market:

Check Out Chicago's Most Expensive Condos For Sale Below:, Over $1,000,000

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3100 N Kenmore Avenue 3j, Chicago

$1,095,000

3100 N Kenmore Avenue 3j, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12765905

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1728 N Sawyer Avenue Rear, Chicago

$1,095,000

1728 N Sawyer Avenue Rear, Chicago

5 Beds 3.5 Baths 3,100 SqFt Residential MLS® # 12703999

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New
211 N Harbor Drive 3206, Chicago

$1,090,000

211 N Harbor Drive 3206, Chicago

2 Beds 2.5 Baths 1,384 SqFt Residential MLS® # 12780484

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211 N Harbor Drive 3209, Chicago

$1,090,000

211 N Harbor Drive 3209, Chicago

3 Beds 2 Baths 1,550 SqFt Residential MLS® # 12713659

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3547 N Reta Avenue 101, Chicago

$1,090,000

↓ $60,000

3547 N Reta Avenue 101, Chicago

4 Beds 2.5 Baths 2,800 SqFt Residential MLS® # 12712780

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1201 S Prairie Avenue 3303, Chicago

$1,090,000

1201 S Prairie Avenue 3303, Chicago

3 Beds 2 Baths 1,746 SqFt Residential MLS® # 12625837

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211 N Harbor Drive 3009, Chicago

$1,080,000

211 N Harbor Drive 3009, Chicago

3 Beds 2 Baths 1,550 SqFt Residential MLS® # 12768188

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211 N Harbor Drive 3006, Chicago

$1,080,000

211 N Harbor Drive 3006, Chicago

2 Beds 2.5 Baths 1,384 SqFt Residential MLS® # 12735043

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New
1648 W Division Street 707, Chicago

$1,075,000

1648 W Division Street 707, Chicago

3 Beds 2.5 Baths 1,915 SqFt Residential MLS® # 12718681

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1120 N Lake Shore Drive 16b, Chicago

$1,075,000

↓ $100,000

1120 N Lake Shore Drive 16b, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12716342

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234 W Polk Street 3704, Chicago

$1,075,000

234 W Polk Street 3704, Chicago

2 Beds 2 Baths 1,535 SqFt Residential MLS® # 12538230

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401 N Wabash Avenue 37c, Chicago

$1,075,000

401 N Wabash Avenue 37c, Chicago

2 Beds 2.5 Baths 1,800 SqFt Residential MLS® # 12305200

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340 E Randolph Street 4802, Chicago

$1,074,999

↓ $24,001

340 E Randolph Street 4802, Chicago

2 Beds 2.5 Baths 1,647 SqFt Residential MLS® # 12725282

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3739 N Clifton Avenue 3, Chicago

$1,065,000

↓ $35,000

3739 N Clifton Avenue 3, Chicago

2 Beds 2 Baths 0 SqFt Residential MLS® # 12703662

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211 N Harbor Drive 2509, Chicago

$1,055,000

211 N Harbor Drive 2509, Chicago

3 Beds 2 Baths 1,550 SqFt Residential MLS® # 12744216

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New Open House
1938 N Sawyer Avenue 1, Chicago

$1,050,000

1938 N Sawyer Avenue 1, Chicago

4 Beds 3.5 Baths 3,200 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12780386

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New Open House
2032 N Burling Street 3, Chicago

$1,050,000

2032 N Burling Street 3, Chicago

3 Beds 3 Baths 0 SqFt Residential
Sun, Oct 11th, 2026 @ 2pm - 3:30pm
MLS® # 12779960

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Open House
2012 W Shakespeare Avenue 1, Chicago

$1,050,000

2012 W Shakespeare Avenue 1, Chicago

4 Beds 3 Baths 2,800 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 1pm
MLS® # 12767134

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Open House
2837 N Halsted Street 2n, Chicago

$1,050,000

2837 N Halsted Street 2n, Chicago

3 Beds 2 Baths 1,650 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 1:30pm
MLS® # 12759219

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1420 N Elk Grove Avenue 2, Chicago

$1,050,000

1420 N Elk Grove Avenue 2, Chicago

3 Beds 2 Baths 0 SqFt Residential MLS® # 12735512

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1757 W Sunnyside Avenue A, Chicago

$1,050,000

1757 W Sunnyside Avenue A, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12732237

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1310 N Ritchie Court 10ad, Chicago

$1,050,000

↓ $99,000

1310 N Ritchie Court 10ad, Chicago

3 Beds 3 Baths 3,000 SqFt Residential MLS® # 12717753

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57 E Delaware Place 1805, Chicago

$1,050,000

↓ $20,000

57 E Delaware Place 1805, Chicago

3 Beds 2.5 Baths 1,855 SqFt Residential MLS® # 12633258

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1345 W Grand Avenue 4n, Chicago

$1,049,999

1345 W Grand Avenue 4n, Chicago

2 Beds 2 Baths 0 SqFt Residential MLS® # 12764213

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Posted by Leo Clark. on

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